As a very young man, Hilary became involved in agriculture. After his military service (he began as a bugler, and received " multiple minor schrapnel wounds" in process of moving materiel in support services) he bought a small orchard and farm at Evesham, Worchestershire, where he spent the rest of his life. JRR's wife and children stayed with him on occasion.

He married Ann Madeline (Magdalen) Matthews in 1928. Their first son, Gabriel, was born in 1931, Julian in 1935, and Paul in 1938.

Hilary Tolkien had a dog which he called Bilbo when it was good, and Baggins when it was bad.[1]